Acetic Acid → 3,5-dimethyl-4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrazole-1-carboxylic acid 4-methoxy-benzylamide

HRID 1024254

반응식

HRID 1024254 반응식
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:17][C:18]2[C:19]([CH3:24])=[N:20][NH:21][C:22]=2[CH3:23])=[CH:9]1)=O)(C)(C)C.[N:25]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[C:26]=[O:27].C(O)(=O)C>ClCCl>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][NH:25][C:26]([N:21]2[C:22]([CH3:23])=[C:18]([CH2:17][C:10]3[C:11]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:8][CH:9]=3)[C:19]([CH3:24])=[N:20]2)=[O:27])=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 187910Isocyanic acid, p-methoxybenzyl-HCID 59593344HCID 59593344, 화합물

생성물 1

HCID 249535763,5-dimethyl-4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrazole-1-carboxylic acid 4-methoxy-benzylamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(3,5-dimethyl-1H-pyrazol-4-ylmethyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (514, 10 mg, 0.03 mmol) was dissolved in dichloromethane (0.5 mL). 1,8-Diazabicylo[5.4.0]unde-7-ene (6 mg, 0.04 mmol) was added. 1-Isocyanatomethyl-4-methoxy-benzene (545, 6.5 mg, 0.04 mmol) was added. The reaction was allowed to proceed at room temperature for 30 minutes. Acetic acid (0.2 mL) was added to the reaction. The solvents were removed under reduced pressure. The residue was dissolved in dimethyl sulfoxide (0.2 mL) and purified by reverse phase HPLC on a Phenomenex column (50 mm×10 mm ID), eluting with water with 0.1% trifluoroacetic acid and 20-100% acetonitrile with 0.1% trifluoroacetic acid over 16 minutes at a flow rate of 6 mL/minute to provide the desired compound P-0135. MS (ESI) [M+H+]+=390.3.

후처리

  1. customThe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in dimethyl sulfoxide (0.2 mL)
  3. custompurified by reverse phase HPLC on a Phenomenex column (50 mm×10 mm ID)
  4. washeluting with water with 0.1% trifluoroacetic acid and 20-100% acetonitrile with 0.1% trifluoroacetic acid over 16 minutes at a flow rate of 6 mL/minute

출처 및 근거

ORD 기록
ord-58eb315e9d0c49b1a399d98137485ca3
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722702B2

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